The Groove Yard
I think that the increasing popularity of the MP3 player, and the advent of "on demand" content leads us to a perfect solution:
The Oldies Podcast.
I know that there are issues with compensating the artist for the music played, so maybe following the model developed by music download sites and the TV networks is the answer:
The 99-cent Oldies Podcast.
A half-hour/hour (depending on rights fees/profit) of your favorite Oldies jock playing great tunes. Save it to your PC and/or MP3 player and put it in the shuffle. Want more? Spend another 99-cents and download another hour of music from a different legendary jock. Collect them all and have the Oldies Station of Your Dreams at your fingertips.
Want free podcasts? Include commercials in the podcast so sponsors pay the costs. They get you three ways - at the website while you're going through the list of available casts, during the download, and while you're playing them back.
Send me the consulting check when the money starts rolling in.
PS - Podcasts of your favorite morning show bits could also be available. Less music, more compensation for the "original artist". No rebates for having to listen to bad Sean Connery impressions.